Your Flex Life

Meet Today’s ‘Anywhere Employees’

New Companies, Greater Freedoms Bring New Meaning To Working Remotely

BY Carly MilneNovember 8, 2018

When Robert McGuire’s wife’s academic research work turned into a long-term project overseas, he found himself unexpectedly living a dream he never planned on: traveling the world while maintaining his robust freelance business.

“No one would look at me and think of me as a person who ‘works abroad,’ but in the last 11 years, I've spent more than 10 percent of my time working abroad, and that's not counting straight-up vacations without work,” McGuire said.

The concept of working remotely is busting free from home offices and breakfast nooks—and heading across the globe thanks to employers and services catering to the “untethered” lifestyle, which is predicated on the ability to work from literally anywhere. And while flexibility in housing, transportation and lifestyle are key enablers for members of this nomadic workforce, they certainly don’t have to go it alone on their off-the-map professional journeys.

New Experiences—And Opportunities


In fact, a handful of young companies have popped up to help this new breed of employee plan and execute the work-abroad lifestyle. Unsettled runs working retreats ranging from two weeks to a month in far-flung locales such as Bali, Nicaragua, Peru and Morocco. For a fee, Unsettled handles everything from housing to travel to a comfortable workspace, along with locally curated experiences to immerse freelancers in the region’s culture.

“It’s almost comparable to a ‘study abroad’ experience for adults,” explained Unsettled co-founder Jonathan Kalan, an award-winning photographer, journalist and media entrepreneur who has traveled to over 70 countries while reporting for the BBC, The Atlantic and The New York Times, among other publications. “People can define work as whatever they want. One person might spend eight hours grinding away, another might be more focused on working on themselves. You can choose your own adventure and explore how you want to explore.”

Every day, there are anywhere from 50 to 100 freelancers using Unsettled to work in 12 different countries. Initially launched as an annual sailing trip between colleagues and friends has now blossomed into a community of remote workers ranging from full-time freelancers to entrepreneurs to people who left the corporate world looking for inspiration on their next move.

“Working abroad can be isolating, which is where a community is nice,” Kalan said. “But it can also be isolating and lonely just like living in New York.”

Another popular option for those looking to freelance abroad is Remote Year, which similarly handles your travel and working arrangements for an up-front payment and monthly fee. Remote Year will even convince the occasional skeptical employer of the productivity and lifestyle benefits of their programs, which include year-long stays in Vietnam, Thailand, Japan, Chile, Colombia, and shorter four-month stints in South Africa, Morocco, Portugal, and Spain.

“Traveling the world and becoming fully immersed in cities that have a unique history and culture is integral to attain the global perspective required in the professional world today,” said Emma Leuman, a Brand Content Specialist at Remote Year.

Remote Year participants represent a broad scope of the workforce, with participants ranging in age from 23 to 72 and representing 40 different nationalities, Leuman said. While employees participating in the program can aid in the reach and globalization of their companies, she said other people turn to Remote Year for reasons that are purely personal, such as overcoming a divorce or going through some other life-altering event. Others simply want to experience the world through the eyes of a local in another country.

“This experience can be life-changing for many participants, as it inspires them to open their eyes to new possibilities for happiness,” Leuman said. “It gives them permission to follow their own path instead of sticking to the status quo.”

The Internationally Unthethered: Who They Are

While the exact size of this new segment of workers is hard to pin down, McGuire, the founder of freelancer resource, has been keeping track of data surrounding the “work abroad” lifestyle—and the numbers are definitely interesting.

He cites a recent And Co survey of such workers that reveals a diversity of purposes and roles in the segment. It found that 64% of survey respondents were true freelancers, while the other 36% were traditional employees working remotely.

One of the more telling statistics reveals that 73% of respondents reported being remote workers for less than four years – a nod to both the movement’s infancy and the idea that it may not be a permanent work solution for most. However, the And Co study—a collaboration with Remote Year – showed that the longer people worked remotely, the more likely they were to try working remotely on a permanent basis.

Kalan said she’s predicting big things ahead for the “work anywhere” crowd, which she terms a movement.

“We’re looking at one of the greatest fundamental shifts in the nature of work since industrial revolution,” Kalan said.

Life Transformations


If the trend has staying power, one of the reasons may well be the dramatic life changes often seen through programs liked Unsettled and Remote Year.

Unsettled’s Kalan recalled a woman using the program to take a sabbatical from her tech startup so she could evaluate her life and career—only to return home to a promotion. Then there was the freelance writer who was able to leverage expertise from the Unsettled community to help her launch an entirely new business. Other members of the community have moved across countries to become business partners with someone they met through Unsettled.

“These things happen all the time,” Kalan said.

Of course, that doesn’t mean there aren’t challenges to surmount in working abroad. McGuire’s issues included a 12-hour time zone difference with clients back home and the spotty electricity and internet that often comes with working in a developing country.

“The main thing is not to get into assignments that are time-sensitive or where the communication needs to be daily and prompt,” he said. “It needs to be okay that the email status update you composed sits in the draft folder for a couple of days.”

McGuire also advised longer stays in a single spot so as not to waste valuable time getting set up in a new location.

Meanwhile, Kalan said it’s important for every “work abroad” enthusiast to define their goals before they go and what they need to be comfortable in the lifestyle, including whether they want to become permanent digital nomads or use the experience as a temporary stepping stone to something more conventional.

“Being a freelancer brings you the opportunity to evolve your skills and your knowledge of yourself,” Kalan said. “So if you take that time and are intentional about how you use it, it becomes a lot easier.”

Despite the challenges, the professional nomad lifestyle remains attractive to most, with 75 percent of employees surveyed in a Softchoice study saying they would quit their job for one that offered remote work.

As to whether it’s right for you, Kalan said you won’t know until you try.

“Nothing is permanent,” he said. “So if you go for it and it’s not for you, you can always do something else.”

As flexible as your life.

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